CAS 138982-67-9 | Ziprasidone Hydrochloride

Properties

Appearance Light Orange solid
Melting point:300°C
storage temp. 2-8°C
solubility DMSO: >10mg/mL

 

Application:

Ziprasidone (CP-88059) hydrochloride is an orally active 5-HT and dopamine receptor antagonist. Suitable for treating schizophrenia

Application Area	Description
Schizophrenia	Acute Treatment: Reduces positive symptoms (hallucinations, delusions) and negative symptoms (apathy, social withdrawal).Maintenance: Prevents relapse and maintains symptom control.
Bipolar Disorder	Mania: Treats manic or mixed episodes associated with bipolar I disorder.Maintenance: Often used as an adjunct to mood stabilizers (like lithium or valproate) to prevent recurrence of mood episodes.

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Related Intermediate Chemicals

         The synthesis of Ziprasidone involves two main fragments that are coupled together: a piperazine moiety and an indole moiety.

Here are the critical intermediates involved in the synthesis:

Intermediate Name	CAS Number	Role in Synthesis
5-(2-Chloroethyl)-6-chloro-1,3-dihydro-indol-2-one	138982-68-0	A mian intermediate representing the indole fragment. It is reacted with the piperazine fragment to form the core structure.
1-(1-Benzothiophen-2-yl)-piperazine	10203-37-5	A main intermediate representing the piperazine fragment. It is the starting material for the side chain or is directly coupled with the indole.
1-(1-Benzothiophen-2-yl)-4-(2-hydroxyethyl)piperazine	138982-70-4	An alcohol intermediate formed by reacting the piperazine with ethylene oxide or similar agents.
2-(4-(1-Benzothiophen-2-yl)piperazin-1-yl)ethyl methanesulfonate	(Variable)	A sulfonate ester intermediate used to facilitate the coupling reaction with the indole group.
6-Chloro-5-(2-((2-(1-benzothiophen-2-yl)piperazin-1-yl)ethyl)-1,3-dihydro-indol-2-one	146939-27-7	The free base form of Ziprasidone (Ziprasidone Base), which is then converted to the hydrochloride salt.

Summary of the Synthetic Route

The standard synthetic route involves:

Fragment A: Synthesizing the indole portion (containing a chloroethyl group) from appropriate aniline derivatives.

Fragment B: Synthesizing the piperazine portion (substituted with benzothiophene).

Coupling: Reacting the chloroethyl-indole (Fragment A) with the benzothiophene-piperazine (Fragment B) via a nucleophilic substitution reaction to form the core molecule.

Salt Formation: Treating the resulting free base with hydrochloric acid to form the final Ziprasidone Hydrochloride.

 

Synonyms:

138982-67-9

Ziprasidone hydrochloride monohydrate

Ziprasidone HCl hydrate

5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hydrate

Zeldox

Ziprasidone (hydrochloride monohydrate)

2H-Indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-, hydrochloride, hydrate (1:1:1)

5-(2-(4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-2-indolinone monohydrochloride, monohydrate

2H-Indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-, monohydrochloride, monohydrate

 

 

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